Retirement Lessons We Can Learn from the Cubs

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Their Win is Your Win

As I sit here and reflect on the Cubs historic World Series win, I find myself still wondering “Did that really happen?” I was born and raised in the Chicago area. I would run home from school just to see the end of that day’s Cubs game on WGN, the local TV station. The Cubs were lousy and I was also a fan of the White Sox (hey, they made it to the World Series in 1959!), but there was something about the ballpark, sunshine and those old fashioned pinstripe uniforms that made them my favorite.

A Lifetime of Championing the Underdogs

Maybe this is why I have pulled for the underdog and hopeless causes my whole life. During my coaching days, I would try to pick out the player having the least fun and see if I could help them to find the joy in playing. Once that happened, they inevitably became better players. Did you notice how much fun the Cubs players were having? They were goofing around on the base paths and in the field as well as in the dugout and clubhouse. For me it just added to the fun and entertainment. Despite the joking around, they still put in hours and hours of practice and study in order to reach their championship, time most of us never see in preparation.

Baseball and Retirement Planning

So, given 108 years of frustration and failure, what changed for the Cubs, and is there anything we can learn from their success and apply it to successful retirement planning? After all, the level of failure achieved by the Cubs franchise was of historical proportions. Many of you who are reading this might feel like there is no possible way to plan and execute a successful retirement, so why should you! try? The Cubs ownership and fans (me included) had just figured that championships weren’t for the Cubs. We could go to the ballpark and have fun, but at the end of the day, there really wasn’t a point. We had all resigned ourselves to the fact the season would just end the same as all the rest; “Cubs lose” and “Wait until next year!” Please don’t let that be your response to creating the retirement of your dreams!

Here are 5 things that changed for the Cubs and how you can put these concepts to work for your retirement:

Number 1
Get out of your comfort zone!Everyone had embraced failure as the inevitable outcome. We could try, even have some success, but in the end it would be futile, another losing season. When the new owner bought the team, he and his group, brought a new perspective and attitude to the team. They say attitude is set at the top and in this case, that is exactly what happened. Tom Ricketts guaranteed that he would bring a World Series Championship to Chicago. He said it out loud and many laughed and were skeptical when he told everyone his goal. I figured he was just another out of touch rich guy who was collecting a trophy (the team) for his collection. By saying this, it forced everyone working for the team to decide if they were on board or not. Belief is a very strong force that will attract all kinds of things to you, both good and bad.

I hear people tell me they will never be able to retire, or they will be struggling in retirement. I think what is really being said is “I don’t know how to be able to retire successfully.” If you aren’t already on track for the comfortable, fulfilling retirement you deserve, then it is time to do something different. Get a different strategy and attitude. The way to do this successfully is to first commit to that thing you want to have a different outcome. For the Cubs, it was setting the intention of winning the World Series and then committing fully to that outcome. If you will do this with your retirement objectives, then it is only a matter of time until you will have that awesome retirement!

Number 2
Hire experts to evaluate options and develop a plan.When the ownership changed and the new owners expressed their intention to change the “wait until next year” mentality of the team, the first move was to hire a new executive to run the operation. They hired Theo Epstein, who had helped changed the way teams are built. He was the executive who had rebuilt the Boston Red Sox and helped them win a world series after many decades of falling short. Theo had the proven knowledge and expertise to strategize and build a team that was capable of winning the championship. Once that was done, he could create a management team that had the individual expertise to execute that vision.

If you aren’t on a path to victory in your retirement planning, hire a financial planner who can help you build your strategy and create a plan that will lead to a “winning” retirement. He or she will help you identify the coaches and experts that will build your management team (tax, legal and investment, or other experts as needed) and put you on the road to realizing your retirement vision.

Number 3
Implement your plan.Once the Cubs put their management team together and solidified their intentions, they could then acquire players who would execute the plan and become that winning organization. Through drafts and trades, over several years, they brought in talent that has taken them to the top of the baseball world. It didn’t happen overnight, but once they knew what kind of team they wanted, they could draft players that fit that concept. They have a lineup of players that are very versatile and can play multiple positions. All major league teams have talent, but the confidence built by using talent (the equivalent of investments and strategies) that fits the vision is the difference in them being a champion or an also ran.

Once you have committed to an outcome, you will find decision making much easier. Pick investments and strategies that fit your personal vision, not someone else’s rule of thumb or must do’s. There are many alternatives to stocks, bonds and mutual funds which can all get you where you want to go. The most important thing is that your choices are consistent with your vision which will lead to confidence and well-being.

Number 4
Don’t fear change, embrace it!As the season progressed, it became apparent that the team had a weakness. Even though they were piling up win after win, management knew that when things got tight, they would need to have a reliable ninth inning pitcher. Most of the time they were winning big, so their success was hiding this fact. Management knew that there would be close games to come, especially in the playoffs. Even though it was controversial at the time, Cubs management went out and got Aroldis Chapman in a trade to be their closer. This ultimately was the difference in winning some very close games in the post season, especially in the World Series. By embracing change and making that move, they were able to separate themselves from everyone else and achieve the championship!

Many times over the years, I have had clients come to me with an asset or strategy that worked for them previously, but were not currently succeeding with that strategy. Despite their acknowledgement that the investment was no longer moving them toward their vision, they were unwilling to change based on what was comfortable previously. For example, a prospective client recently came in with concerns that their income wasn’t going to be enough to support their lifestyle. For business and family reasons, they were going to be moving in a few years to the east coast. They had paid off their mortgage and had equity in their home well over a million dollars, yet were struggling to pay taxes and utilities, much less buy food and have some entertainment. Before even bringing up the subject they told me they would never sell the house, because they wanted their kids to get it. Even after pointing out the fact that her 2 children couldn’t live there together and would likely have to sell it, she insisted that they would be the ones to make that decision, even though she may ultimately be forced to sell because she can’t afford to maintain the house. If she would embrace the change of selling and moving, she would have more than enough to create the income she needs to enjoy the lifestyle she wants.

Number 5
Keep your eye on the prize. Baseball seasons are like novels. When you begin, you think you know where the story is going. Inevitably, due to the length of the season, twists and turns will come up. Players will slump, others will be injured and still others will become ineffective just because of age. Players get optioned, acquired and “sent down to the minor league.” When the season begins, you can’t know where these issues will come from, or how severe they will be, just that the twists and turns will be part of the story. To be successful, the team must have some contingencies built into their plans to be able to make adjustments to deal with the challenges as they arise. Even then, there will be things that come up which weren’t anticipated. By being clear on their objectives and building everything toward that, these distractions won’t grow into derailments.

When you are building your retirement plans, make sure you acknowledge that there will be bumps along the way. Interest rates will change, markets drop, tenants default and many other distractions will come your way. By maintaining focus and clarity about what you are after, these distractions will fade away and will hardly amount to anything in the grand scheme of things.

You Too Can Have a Winning Season and a Happy Retirement

Following these guidelines will put you on the road to a happy retirement. If you would like to investigate whether I can help you build your vision and your team to achieve it, or just want to discuss your vision and have some help putting it in focus, contact us and we will do what we can to help you out.

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